This paper presents a case study on the analysis of psychological demand conducted within a training and support intervention requested by a regional office of the Italian Penitentiary Administration for its personnel. The six-month project involved six managerial figures and eight operators through individual semi-structured interviews and a focus group. Text analysis, carried out using the T-LAB software and based on the collusive processes model, identified six thematic clusters related to organizational issues (fragmentation, inconsistency) and relational resources (peer support). The intervention activated a space for intersubjective reflection and enabled a reformulation of the initial request as an opportunity for shared meaning-making, fostering the development of a change-oriented planning process.